Hydrochloric Acid → 2-(2-Oxopyrrolidin-1-yl)pent-4-enoic acid

HRID 1391705

反応式

HRID 1391705 の反応式
[Li+].[OH-].[O:3]=[C:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH:9]([CH2:14][CH:15]=[CH2:16])[C:10]([O:12]C)=[O:11].Cl>O.C1COCC1>[O:3]=[C:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH:9]([CH2:14][CH:15]=[CH2:16])[C:10]([OH:12])=[O:11]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58813161Methyl 2-(2-oxopyrrolidin-1-yl)pent-4-enoate

生成物 1

HCID 588131062-(2-Oxopyrrolidin-1-yl)pent-4-enoic acid収率 81.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Step A (2): A solution of LiOH (2 M, 0.73 g, 30.4 mmol) in 15 mL H2O was added to a solution of methyl 2-(2-oxopyrrolidin-1-yl)pent-4-enoate (2.0 g, 10.1 mmol) from step A(1) in THF (15 mL) at room temperature. The mixture was stirred at room temperature for 16 h. Poured into 1 N HCl. Extracted with EtOAc (3×250 mL). Washed combined organics with brine, dried with Na2SO4 After concentration in vacuo, dried on high-vacuum for ˜3 h to give 1.5 g (81%) of 2-(2-oxopyrrolidin-1-yl)pent-4-enoic acid as a beige solid: LC-MS (M+H)+=184.1; 1H NMR (300 MHz, CDCl3) δ 11.85 (s, 1H), 5.47-5.81 (m, 1H), 4.91-5.25 (m, 2H), 4.81 (dd, J=11.14, 4.73 Hz, 1H), 3.45-3.59 (m, 1H), 3.25-3.40 (m, 1H), 2.59-2.83 (m, 1H), 2.30-2.52 (m, 3H), 1.80-2.12 (m, 2H).

後処理

  1. extractionExtracted with EtOAc (3×250 mL)
  2. washWashed
  3. dry with materialdried with Na2SO4
  4. concentrationAfter concentration in vacuo
  5. customdried on high-vacuum for ˜3 h

出典と根拠

ORDレコード
ord-bd2912246b39480cad20c89bf5a4d143
出典データセット
uspto-grants-2008_03
特許番号
US07338974B2

関連ノート

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